Annual Events

All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor movies under the stars, a festive parade down Main Street, a food truck festival with great live music…these are all events you can experience for yourself right here in Middlebury every year. Check them out!

Summer

Foodaroo
Food truck festival featuring live entertainment

Vermont Gran Fondo
A challenging four-peak cycling event

Middlebury Summer Music & Movie Series
Outdoor movies and live concerts throughout the summer

Festival on the Green
A week-long free concert series on the town green

Sheldon Museum Pops Concert
Fireworks and concert to celebrate the 4th of July

St Stephen’s Peasant Market
The area’s largest flea market and rummage sale

Lion’s Club Auction
Auction and BBQ on the green

Downtown Block Party
A festive party on the closed off streets of Downtown Middlebury

Ciderstock
Annual music festival at Woodchuck Cider House

Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers

Fall

Spooktacular
Trick-or-Treating down Main Street

Turkey Trot
Scenic 5k and 10k before Thanksgiving

Winter

WinterFest
Middlebury’s celebration of all things winter

Very Merry Middlebury
A month-long celebration of the holidays

Midd Night Stroll
Extended evening shopping, tasting and strolling

Spring

Middlebury Maple Run
A half marathon and fun run with the sweetest views

Memorial Day Parade
Marching bands, floats and more down Main Street